A. Field of the Invention
This invention relates to novel quaternary ammonium antimicrobial compounds and their use.
B. Description of the Prior Art Quaternary ammonium compounds having the general formula (A): ##STR3## wherein R.sub.1, R.sub.2, and R.sub.3 are all substituted or unsubstituted carbon chains were disclosed in U.S. Pat. No. 4,521,412 as having antifungal and antibacterial activity.
Tropium quaternary ammonium compounds having the general structure (B): ##STR4##
wherein X=chlorine were evaluated for hypotensive activity in J. Org. Chem., 24, 1607 (1959). No antimicrobial activity was mentioned in this paper.
The chloride salt and saccharinate salt of tropium (C) (i.e. X=saccharine) were mentioned in U.S. Pat. No. 4,521,412. ##STR5##
Cyclic quaternary ammonium compounds which do not contain an iodopropargyl group have been disclosed in J. Pharmacol. Exptl. Therap., 121, p.347 (1957), where piperazine mono-quaternary salts were shown to have activity against mouse pinworm.
U.S. Pat. No. 4,233,055 discloses substances of the following general structure (D) for inhibiting the growth of plants and for promoting the ripening and abscission of fruit. ##STR6##
R=alkyl, alkenyl, alkynyl
Cyclic quaternary ammonium compounds have been claimed to be used as surface active agents, bactericides, biocides, algicides or fungicides, as exemplified by the following: ##STR7##
DD-278-268-A, Fungicides ##STR8##
U.S. Pat. No. 4,472,412 (1984), Fungicides ##STR9##
U.S. Pat. No. 3,506,666 (1970), For the control of algae, bacteria and fungi. ##STR10##
U.S. Pat. No. 2,971,006 (1961), claimed to be used as surface active agents, bactericides, biocides, and particularly as fungicities.
Japanese Patent 67-026603B discloses a method of producing 3-halo-2-propynylamines of the formula
(R.sub.1)(R.sub.2)N--CH.sub.2 CC--X
in which R.sub.1 and R.sub.2 may be joined to form a saturated cyclic 6-membered piperidine or morpholine ring.